N,N-Diethylaniline → 4'-{[4-(1,4-Dioxaspiro[4.5]dec-8-yl)-2-methyl-5-oxo-7-propyl-4,5-dihydro[1,2,4]triazolo[1,5-a]pyrimidin-6-yl]methyl}-4-fluorobiphenyl-2-carbonitrile

HRID 2062563노트

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HRID 2062563 반응식
[C:1]([C:3]1[CH:8]=[C:7]([F:9])[CH:6]=[CH:5][C:4]=1[C:10]1[CH:15]=[CH:14][C:13]([CH2:16][CH:17]([C:23](=O)[CH2:24][CH2:25][CH3:26])[C:18](OCC)=[O:19])=[CH:12][CH:11]=1)#[N:2].[O:28]1[C:32]2([CH2:37][CH2:36][CH:35]([NH:38][C:39]3[NH:43][C:42]([CH3:44])=[N:41][N:40]=3)[CH2:34][CH2:33]2)[O:31][CH2:30][CH2:29]1.N12CCCN=C1CCCCC2.C(N(CC)C1C=CC=CC=1)C>C(OCC)(=O)C>[O:28]1[C:32]2([CH2:33][CH2:34][CH:35]([N:38]3[C:18](=[O:19])[C:17]([CH2:16][C:13]4[CH:12]=[CH:11][C:10]([C:4]5[C:3]([C:1]#[N:2])=[CH:8][C:7]([F:9])=[CH:6][CH:5]=5)=[CH:15][CH:14]=4)=[C:23]([CH2:24][CH2:25][CH3:26])[N:40]4[N:41]=[C:42]([CH3:44])[N:43]=[C:39]34)[CH2:36][CH2:37]2)[O:31][CH2:30][CH2:29]1

참가 물질

6

반응물 4

HCID 7061N,N-DiethylanilineHCID 811841,8-Diazabicyclo(5.4.0)undec-7-eneHCID 67009984Ethyl 2-[(2'-cyano-4'-fluorobiphenyl-4-yl)methyl]-3-oxohexanoateHCID 178434101HCID 178434101, 화합물

생성물 1

HCID 670100244'-{[4-(1,4-Dioxaspiro[4.5]dec-8-yl)-2-methyl-5-oxo-7-propyl-4,5-dihydro[1,2,4]triazolo[1,5-a]pyrimidin-6-yl]methyl}-4-fluorobiphenyl-2-carbonitrile수율 52%

시약·촉매·용매 1

HCID 8857Ethyl Acetate용매

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온도
180 °C

실험 절차

A mixture of ethyl 2-[(2′-cyano-4′-fluorobiphenyl-4-yl)methyl]-3-oxohexanoate (2.9 g), N-(1,4-dioxaspiro[4.5]dec-8-yl)-5-methyl-4H-1,2,4-triazol-3-amine (0.93 g), 1,8-diazabicyclo[5.4.0]undec-7-ene (0.29 mL) and N,N-diethylaniline (30 mL) was stirred at 180° C. for 16 hr. The obtained reaction mixture was diluted with ethyl acetate, washed 3 times with 1 N hydrochloric acid and saturated brine, and dried over anhydrous magnesium sulfate. The solvent was evaporated under reduced pressure, and the residue was purified by silica gel column chromatography to give the title compound as a colorless solid (1.1 g, 48%).

후처리

  1. customThe obtained reaction mixture
  2. washwashed 3 times with 1 N hydrochloric acid and saturated brine
  3. dry with materialdried over anhydrous magnesium sulfate
  4. customThe solvent was evaporated under reduced pressure
  5. customthe residue was purified by silica gel column chromatography

출처 및 근거

ORD 기록
ord-07a463ec93e741c28f3775f07e44254c
출처 데이터셋
uspto-grants-2012_10
특허 번호
US08283353B2

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